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In a May 2011 interview for the Financial Times, the “Bad Romance” singer said that her hugely popular world tour, Monster Ball, left her bankrupt after its first leg. “I put everything in the show,” she told interviewer Stephen Fry. It included multiple costume changes, elaborate set designs, and reportedly, quite a bit of experimenting and reformatting. She recalled being astonished to learn that she was three million dollars in debt (“This is ridiculous, I have five number-one singles,” she said), but fortunately for her, the tour was so successful that she earned the money back. Gaga claims not to care about money in the interview, though she did buy her parents a Rolls Royce simply because their old license plate that said “Lady Gaga” on it annoyed her. Wouldn’t a quick phone call to the DMV have cost much less?
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One might assume that Trump, with his sprawling, ostentatious empire, could never run out of money. That might be true of the man himself, but his businesses are another story. In fact, properties and companies under his name have filed for bankruptcy in 1991, 1992, 2004, and 2009. (All that gold-plating in his hotels must’ve added up fast.) Ironically, when he made a move toward a presidential nomination in April 2011, he boasted that his business savvy—as evidenced by his sizable bank account—could save the economy. “I have a much bigger net worth … my net worth is many, many, many times Mitt Romney’s,” he said in an April 2011 interview. Hmm ...you think he’s really talking about bank accounts?
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Those deep in debt should take heart—the Great Emancipator himself was in the same sad spot back in 1833, when he was just a young entrepreneur dealing with his struggling general store in Illinois. Lincoln sold his share of the business, but after his partner died, he became responsible for a whole new share of debts. It took him until the 1840s to pay off the back payments, and then two decades later, he became this country’s sixteenth president. It just goes to show that debt doesn’t always stop you from achieving your dreams.
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During the late 1980s and early ‘90s, MC Hammer was at the top of the music world, having scored moneymaking hits with “U Can’t Touch This” and “Too Legit to Quit.” He celebrated his good fortune by spending a whole lot of it—a twenty-room mansion here, a whole wardrobe of jazzy “Hammer pants” there. The good times came to an end when the rap star filed for bankruptcy in 1996. Years of struggle followed, and in 1997, Hammer joined the ministry, feeling that his lack of faith and out-of-whack priorities had led to his financial demise. Today he’s entered the social media market and has launched a dance site called DanceJam. However, his money woes aren’t too far behind him—in 2009, his tax bills added up to over $600,000.
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Basinger filed for Chapter 11 in May 1993, shortly after she lost a breach-of-contract lawsuit filed against her by the producers of a movie called Boxing Helena. After she backed out of starring in the flick and Main Line Pictures went after her for millions of dollars, she declared bankruptcy, arguing that she lacked the necessary assets to cover the payment. As a result, Basinger had to sell Braselton, Georgia, a town she invested in for twenty million dollars in 1989.
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When Tyson filed for bankruptcy in 2003, he claimed that he had “been in financial distress since 1998,” citing taxes and lawsuits as the main money vacuums. Information on his many creditors was leaked to the press soon after—making it obvious that Tyson also had a ludicrous spending habit. Aside from the almost eighteen million dollars he owed in taxes, the infamous boxer also had hefty tabs at jewelers, limousine services, car dealerships, and other luxury businesses. Despite boxing matches being the proposed source of future income in his bankruptcy deal, he hung up his gloves in 2005. These days, he’s converted to a vegan diet, has a show on Animal Planet called Taking on Tyson, and claims to live paycheck to paycheck.
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Things started going downhill for Reynolds after his messy divorce from Loni Anderson in 1993. The legal fees and settlement, as well as a series of bad investment choices, a lack of interest from movie producers, and sluggish performances at the box office, led the one-time Hollywood powerhouse to declare bankruptcy in 1996. At the time, Reynolds was ten million dollars in debt, but by 1998, he emerged from bankruptcy—the same year he won an Oscar and a BAFTA for Best Supporting Actor in Boogie Nights.
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Even being one of the most famous writers in history doesn’t save you from money problems. Twain’s major downfalls were the failure of his publishing house and his investment in a typesetter machine that never quite lived up to its promise of ingenuity and efficiency. Much of his book profits went into fixing and attempting to perfect the Paige typesetter machine, but it proved to be a money pit that led Twain to declare bankruptcy in 1894. He embarked on a speaking tour around the world a year later in an attempt to pay off his debts, which he finally did in 1898.